Most watch advice is written for buyers. The sell decision gets treated as an afterthought: forum posts thick with sentiment, vague talk about "the right time to sell," and almost nothing from people who buy and work with watches for a living. After thirty years on the buy side of this market, we've seen the same patterns repeat. Sellers who held six months too long. Sellers who panicked out of a dip that corrected in nine months. Sellers who left real money on the table because they didn't understand how the channel they chose actually worked. Today we're giving our advice on how to view sales decisions if the time does come.The Question Nobody Answers WellThe standard advice splits into two primary camps. The sentimental group says: only sell if you no longer love a watch while the emotionally disconnected segment argues to wait for the optimal market conditions. Neither helps a collector who loved their Daytona when they bought it, still loves it now, and is watching it trade at half its 2022 price while wondering whether to hold or exit.